Tracked deals
20
20 tracked deals across 2019-2026.
Real Estate Buyers & Acquisitions in Illinois
Buyer mix
Strategic-led
20 strategic · 8 pe
Top trend
Volume peaked in 2023
4 tracked deals announced in 2023.
Primary Insight
What Stands Out
- Property management remains a dominant thread, including platform building and portfolio expansion by buyers such as Proper, Westward360, and Second Home Management.
- Illinois activity includes both operating-company acquisitions (e.g., management and service platforms) and facility-level asset deals (e.g., self-storage in multiple Chicago neighborhoods).
- Buyers appear to pursue Midwest presence strategically—such as second/entry acquisitions tied to specific Illinois geographies (e.g., Lake County, Chicago neighborhoods).
- Residential real estate services are represented through brokerage infrastructure acquisitions, including Compass, Inc. acquiring @properties.
- Some transactions are framed as technology- and operations-focused platform moves, such as multifamily property management platform launches and tech-enabled property services expansion.
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Top Buyers
Illustrative buyers pulled from tracked transactions on this page. This table is capped and intentionally non-exhaustive.
| Buyer | # Deals | Focus | Type |
|---|---|---|---|
| Westward360 | 2 | Provider of property management and real estate services ... | Strategic |
| 3STEP Sports | 1 | National youth sports club and event operator running clu... | Strategic |
| American Homes 4 Rent | 1 | Public single-family rental REIT and owner/operator of si... | Strategic |
| Berkadia | 1 | Commercial real estate capital markets, mortgage banking ... | Strategic |
| Compass, Inc. | 1 | National real estate technology company and the largest U... | Strategic |
| Fifth Wall | 1 | Venture/strategic investor focused on real estate technol... | PE |
| Flyhomes | 1 | Real-estate technology and services company offering brok... | Strategic |
| Home365 | 1 | PropTech company offering the OneRate platform that guara... | Strategic |
| Invitation Homes | 1 | Public single-family rental REIT and large owner/operator... | Strategic |
| Jones Capital | 1 | Provider of private capital to middle‑market businesses f... | Investor |
Acquisition Volume in Real Estate in Illinois by Year
Last 8 years
Actual
Full-year estimate
Supporting Data
Recent Transactions
-
February 26, 2026
- Buyer
- Proper
- Target
- Novo Properties, Alexander Properties Group (APG), FLATS, Guardian, CommonPlace, Drexel
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Addon
Proper, a national acquisitions and property management platform, announced the successful acquisition of two additional operating companies—Novo Properties and Alexander Properties Group (APG)—bringing its total acquired portfolio to six companies. The combined acquisitions expand Proper’s property management footprint to nearly 20,000 units across 15 states.
-
January 21, 2026
- Buyer
- Outrig
- Target
- Lakes Region Business Rentals
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Buyout
Outrig has acquired Lakes Region Business Rentals, a multi-building small-bay industrial facility in Lakemoor, Illinois, and will rebrand it as Outrig Commerce Park Lakes Region. The acquisition expands Outrig’s small-bay industrial and storage portfolio and strengthens its presence in Lake County, Illinois, where this becomes its second acquisition.
-
- Buyer
- Westward360
- Target
- The Apartment Source (property management division)
- Seller
- The Apartment Source
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Divestiture
Chicago-based Westward360 has merged with The Apartment Source's property management division, assuming management responsibilities while allowing The Apartment Source to focus on multifamily leasing. The transaction expands Westward360's Chicago-area portfolio and market reach while enabling TAS to concentrate on its core leasing business.
-
January 28, 2025
- Buyer
- Peoples Company
- Target
- Land Pro LLC
- Seller
- Ray Brownfield
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Buyout
Peoples Company has acquired Oswego, Illinois-based Land Pro LLC effective January 1, 2025. Land Pro LLC and owner Ray Brownfield became an affiliate of Peoples Company and will continue operating under the Land Pro name while gaining access to Peoples Company's technology, capital markets resources, and expanded Illinois presence.
-
January 14, 2025
- Buyer
- Compass, Inc.
- Target
- @properties
- Seller
- Quad-C Management, Inc.
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Buyout
Compass, Inc. has purchased Chicago-based real estate services firm @properties from Quad-C Management. The acquisition brings @properties' brokerage network, title and mortgage businesses, Christie's International Real Estate affiliation and proprietary technology platform into Compass's national residential brokerage platform.
-
December 5, 2024
- Buyer
- Storage Post Self Storage
- Target
- Self-storage facility — Albany Park (3215 W. Lawrence Ave., Chicago, IL), Self-storage facility — Belmont (2051 N. Austin Ave., Chicago, IL), Self-storage facility — Edgewater (6331 N. Broadway, Chicago, IL), Self-storage facility — Little Village (3245 W. 30th St., Chicago, IL), Self-storage facility — Uptown (5145 N. Clark St., Chicago, IL)
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Buyout
Storage Post Self Storage has acquired five existing self-storage facilities across Chicago neighborhoods (Albany Park, Belmont, Edgewater, Little Village and Uptown), marking the company's entrance into the Midwest market. The acquisitions expand Storage Post's multi-state portfolio and bring its amenity-focused, climate-controlled storage product to the Chicagoland area.
-
- Buyer
- TriSpan, ProperXPM Holdings, LLC
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Buyout
TriSpan has partnered with industry veteran Brian Duggan to launch ProperXPM, a PE-backed residential multifamily property management platform focused on consolidating property managers nationwide. ProperXPM will grow organically and through acquisitions, leveraging a technology partnership with Livly to deliver centralized, tech-driven operational services and improve NOI for building owners.
-
December 22, 2023
- Buyer
- Shore Capital Partners
- Target
- Bundled Management
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Growth capital
Shore Capital Partners has formed a growth partnership with Bundled Management, a national property management platform founded in 2018 that provides property management, maintenance, and ancillary services to homeowner associations and real estate investors. The investment will support Bundled’s national expansion, technology enhancement, and team development as Shore works with Bundled’s leadership and a newly assembled board to scale the business.
-
September 11, 2023
- Buyer
- Flyhomes
- Target
- Home Sale Assured
- Seller
- Innovative Holdings, LLC
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Divestiture
Flyhomes has entered a definitive agreement to acquire certain assets and the Home Sale Assured brand from Innovative Holdings, LLC. The deal brings Home Sale Assured founder Eric Meadow into Flyhomes in a senior executive role and expands Flyhomes' "buy before you sell" Guaranteed Backup Contract offering for lenders, realtors and consumers.
-
- Buyer
- Lessen, Monroe Capital, Värde Partners, Koch Real Estate Investments, Invitation Homes, American Homes 4 Rent, Fifth Wall
- Target
- SMS Assist
- Seller
- SMS Assist stockholders
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Buyout
Lessen has acquired SMS Assist in a cash-and-stock transaction backed by roughly $500 million of new debt and equity financing from investors including Monroe Capital, Värde Partners and Koch Real Estate Investments. The combination creates a national, tech-enabled property services platform serving ~250,000 properties and processing ~2.5 million maintenance orders annually, with Lessen founder Jay McKee leading the combined company.
-
January 12, 2023
- Buyer
- Second Home Management
- Target
- AllSet Turnover
- Seller
- Billy Quaranto (owner, co-founder and president)
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Buyout
Second Home Management has acquired AllSet Turnover, a Chicago-based short-term rental management company founded in 2014 that managed more than 150 rental units. Raincatcher and AJL Atelier advised and represented AllSet in the sale. The acquisition expands Second Home Management's platform presence and local capabilities in the Chicago market.
-
August 9, 2022
- Buyer
- 3STEP Sports
- Target
- Sports Made Personal
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Addon
3STEP Sports has acquired Sports Made Personal (SMP), an Illinois-based youth sports organization that operates soccer and lacrosse clubs, leagues, events, travel and technology offerings. The deal brings SMP's clubs and technology into 3STEP's national platform while retaining SMP's leadership and staff to expand 3STEP's presence in the Midwest.
-
June 23, 2022
- Buyer
- Home365
- Target
- Paper Street Realty
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Buyout
Home365, a San Jose-based PropTech platform, acquired Paper Street Realty to support management of its Chicago real estate investments and expand its OneRate NOI-backed offering into the Chicago market. The acquisition brings Paper Street's local team and management of more than 500 units into Home365's end-to-end property management and investment platform, enabling geographic expansion and local operational capability in Chicago.
-
October 1, 2021
- Buyer
- Zillow Group
- Target
- ShowingTime
- Seller
- Accel-KKR
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Buyout
Zillow Group announced the acquisition of ShowingTime, an online home showing scheduling platform and Accel-KKR portfolio company, for $500 million. ShowingTime will continue to operate as an open platform under Zillow and Zillow plans to invest in and integrate ShowingTime's touring technology to improve scheduling and touring experiences for agents and consumers.
-
September 21, 2021
- Buyer
- Stellus Capital Management, LLC, LBC Small Cap SBIC, LP, Jones Capital
- Target
- Elmdale Partners
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Growth capital
Stellus Capital Management led a strategic growth capital investment in Elmdale Partners, with participation from LBC Small Cap SBIC and Jones Capital. The funding will support Elmdale’s geographic expansion, M&A activity, technology upgrades for its network of independent agents, and refinancing of existing debt.
-
August 11, 2021
- Buyer
- Spruce
- Target
- The Minte
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Buyout
Spruce, a provider of lifestyle services to the multifamily sector, has acquired Chicago-headquartered housekeeping startup The Minte to expand its housekeeping and on-demand chores offering and enter the Chicago market. The deal makes Chicago Spruce's 14th market and gives The Minte greater scale and access to Spruce's logistics and property-management partnerships.
-
January 14, 2021
- Buyer
- Berkadia
- Target
- Moran & Company
- Seller
- Moran & Company
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Divestiture
Berkadia acquired the apartment brokerage practice of Moran & Company, integrating a 31-member team (including 15 institutional sales advisors) and launching Berkadia Institutional Solutions, powered by Moran. Moran Co-Chairman Mary Ann King will join Berkadia as Co-Head of Investment Sales to lead the integration and expansion of Berkadia’s institutional investment sales capabilities.
-
December 15, 2020
- Buyer
- Move, Inc., News Corp
- Target
- Avail
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Buyout
Move, Inc., operator of realtor.com and a News Corp subsidiary, acquired Chicago-based Avail, a platform serving DIY landlords and renters with online rental management tools. The acquisition expands realtor.com's capabilities and audience in the residential rental market by integrating Avail's listing content, workflow tools and customer base into realtor.com's platform.
-
- Buyer
- Westward360
- Target
- Pabcor Management
- Seller
- Pabcor Management
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Buyout
Chicago-based property manager Westward360 has acquired the community association managed portfolio of Pabcor Management, expanding its footprint in the northwest Chicago suburbs around Prospect Heights, Illinois. The deal adds several thousand residential units to Westward360's portfolio, brings some Pabcor staff into Westward360, and supports local growth and operational efficiencies.
-
- Buyer
- Long Ridge Equity Partners
- Target
- Neighborhoods.com (parent of 55places.com)
- Industry
- Real Estate
- Location
- Illinois, United States
- Type
- Growth capital
Long Ridge Equity Partners made a growth capital investment in Neighborhoods.com, the parent company of 55places.com, becoming the company's first outside investor. Long Ridge principals Angad Singh and Dan Hang will join the board to support product and market expansion as Neighborhoods.com pursues adjacent verticals and continued growth of its online real estate marketplaces.
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Frequently Asked Questions
What types of real estate deals appear most in Illinois?
The page highlights property management platform acquisitions (including operating companies and management divisions) alongside facility-level real estate assets like self-storage and residential services such as brokerage infrastructure.
Which buyers show up repeatedly across Illinois deals?
Recurring names include Westward360, Berkadia, Long Ridge Equity Partners, Outrig, Spruce, Flyhomes, Compass, Inc., and Peoples Company.
Do the acquisitions focus only on one Illinois metro area?
No. The page includes deals tied to Chicago and specific suburbs/neighborhoods, as well as other Illinois locations such as Lakemoor and Oswego.
Are there deals beyond property management on the page?
Yes. Examples include Storage Post Self Storage expanding into Chicago self-storage neighborhoods and Compass, Inc. acquiring @properties (brokerage and related real estate services).
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